Hello Tom,
The 9.9 was already on my boat when I purchased it. It is a high thrust Yamaha engine. It pushes the Stiletto amazingly quick for its size. It is pretty heavy though about 100#s. If I were to purchase one I would probably get an 18 hp with the same weight. Some have told me there is no difference between the 2 except maybe carb. and small displacement. For typical lake sailing the waves won't be too large so you would only have to deal with the wind.
I use the standard motor mount with a wave deflector that I built (see the portfolio section of the Stiletto website) When I take the boat down the motor is mounted onto a cross rail on the trailer. It is mounted just like it sits on the back ob the boat except straight out but I paded the mount and have had no problem.
One of the Stiletto's in LC has a Merc. 25 4 stroke, I think the weight is close to the Yamaha. I wouldn't go larger because of the weight sticking out the back. The 4 stroke is much more fuel efficient than a 2 stroke (less polutants too). A comparison on a trip out of LC had 2 Stilettos one with the 25 Merc. and one with a 15 Merc. 2 stroke (a weekend trip down to the gulf) the smaller engine used an extra tank of fuel (6 gallons). Of course your mileage may vary, not available in all states, 1 available per customer (no wait that is something else)...
Does this help?
Clayton